My revised map of the town of Winterhaven in the universe of D&D 4E. The town of Winterhaven as presented in the official materials has a grand total of 15 buildings in it.

(you can see the official town map here in my scrapbook, if you're curious: [link])

Fifteen! How are people supposed to have an exciting adventure in the town like that?

In my re-design of Winterhaven, I increased the overall scale of the settlement and added a lot more buildings. I tried to imagine the original town as a jumping-off point, and then built new structures in as though the townspeople themselves had enlarged their community over time, deconstructing the old walls and rebuilding new walls around the old city center. I also made it a LOT less orthogonal. This would make it more difficult to play on if the players were using the grid here, but it's really just a piece of the Overworld map, and battles aren't really meant to spring out on the streets of the overworld.

To be fair, in the official history of Winterhaven in the core books, it started its life as a walled fort along the main road, only becoming a small town after the end of the war about 90 years ago. Walled forts usually do have small, boring, right-angled plans, so it made more sense than my version maybe. But it still wasn't any fun to look at.